2-alkoxypropenals as synthetic equivalents of methylglyoxal in the synthesis of heterocycles

• Published in: Russian journal of organic chemistry Vol. 49; no. 3; pp. 428 - 431
• Main Authors: Keiko, N. A., Vchislo, N. V., Larina, L. I.
• Format: Journal Article
• Language: English
• Published: Dordrecht SP MAIK Nauka/Interperiodica 01-03-2013
• Subjects: Chemistry; Chemistry and Materials Science; Organic Chemistry; Methylglyoxal; Quinoxaline; Synthetic Equivalent; Enediamine; Weakly Acidic Medium
• ISSN: 1070-4280; 1608-3393
• DOI: 10.1134/S1070428013030196

One-pot synthesis of 2-methylquinoxaline, 3-hydroxy-2-methylimidazo[1,2-
a
]pyridine, and 2-methyl-3,7-dihydroimidazo[1,2-
a
]pyrazin-3-one via cycloaddition of N,N-binucleophilic
o
-phenylenediamine, 2-aminopyridine, and 2-aminopyrazine, respectively, to methylglyoxal generated
in situ
by hydrolysis of 2-alkoxypropenals is reported for the first time. Thus 2-alkoxypropenals in weakly acidic medium (25–80°C, 1–4 h) are convenient synthetic equivalents of methylglyoxal in the synthesis of heterocyclic compounds.